Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 1 of 14 **UNITED STA TES ENVIRONMENTA**  **L PROTECTION A GENCY** 

WA SHINGTON, D.C. 20460 **OFFICE OF CHEMICAL SAFETY AND**  **POLLUTION PREVENTION MEMORANDUM**  **Date** : 04 - AUG - 2011 **Subject** : **Saflufenacil** in/on Imported Coffee, Banana, and Mango . **Summary of Analytical**

**Chemistry and Residue Data**  . **PC Code:** 118203 **DP Barcode:** D 390922 **Decision No.:** 4 42242 **Registration No :**  NA **Petition No .**  **:** 0E7806 **Regulatory Action:** Tolerances With No U.S. Registration **Risk A**  **ss essment Type**  **:** NA **Case No.:**  NA **T XR No.**  **:** NA **CAS No.:** 372137 - 35 - 4 **MRID No s**  **. :**  482398 - 01 thru - 0 7 **40 CFR:** §180. 649 **From** : George F. Kramer, Ph.D., Senior Chemist

Risk Assessment Branch 1 (RAB1) Health Effects Division (HED) (7509P) **Through** : Dana M. Vogel , Branch Chief

RAB1/HED (7509P) **To** : Kathry

n Montague/ Susan Stanton , PM Team 23 Registration Division (RD; 7505P) **Executive Summary** Saflufenacil (BAS 800 H) is a broad - spectrum herbicide developed by BASF. It belongs to the herbicide mode - of

- action Group 14 (cell membrane disruptors). Saflufenaci l acts through the inhibition of protoporphyrinogen oxidase (PPO), resulting in cell membrane damage and subsequent plant death. SharpenTM Powered b y Kixor Herbicide (EPA Reg. No. 7969 - 278), a 2.85 lb ai/gal suspension - concentrate (SC) formulation, is currently registered for use on legume vegetables (Crop Group 06), the foliage of legume vegetables (Crop Group 07), cereal grains (Crop Group 15), the forage, fodder, and straw of cereal grains (Crop Group 16), cotton, and sunflower. BASF has submitted a p roposal to establish tolerances for saflufenacil in/on imported coffee, banana, and mango (PP#0E7806). The tolerance petition on these crops is the result of the use of Heat ® , a 70% water - dispersible granule (WDG) formulation, in Central and South America . Heat ® is proposed for up to three foliar spray applications directed to the base of the plants with a total maximum application rate of 0.131 lb ai/A, and use of an adjuvant is required. Preharvest intervals (PHIs) of 7 - 30 day s are proposed.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 2 of 14 BASF ha s petitioned for the establishment of permanent tolerances for “saflufenacil, including its metabolites and degradates, in or on the imported agricultural commodities listed below. Compliance with the tolerance levels specified below is to be determined b y measuring only the sum of saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2H ) - py rimidinyl] - 4 - fluoro -N

- [[methyl(1 - methylethyl)amino]sulfonyl]benzamide, and its metabolites N - [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl ) - 3,6 - dihydro - 1(2H ) - py rimidinyl) - 4 - fluorobenzoyl] - N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbonyl )phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil” in/on the following raw agricultural commodities (RACs):

Coffee, green bean 0.03 ppm Banana, whole fruit 0.03 ppm Mango, fruit 0.03 ppm The previousl y- submitted metabolism data for corn, soy bean, and tomato were adequate to elucidate the nature of the residue in plants resulting from pre - plant/pre - emergence application. The HED Residues of Concern Knowledgebase Subcommittee (ROCKS) determined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 (Memo, B. Daiss, 1/6/09; D 359645 ). This conclusion was translated to perennial crops (i.e., tree fruits and tree nuts) where saflufenacil application is directed to the weeds on the orchard floor (Memo, G. Kramer, 7/22/09; D 349938 ). As the proposed use on coffee, banana, and mango is also directed to weeds at the base of the plants, HED concludes that the residues of concern for the tolerance expression and risk assessment also consist of saflufenacil, M800H11, and M800H35 for these crops. The nature of the residue in livestock is adequately understood based on acceptable metabolism studies conducted on lactating goats and laying hens. There are no livestock feedstuffs associated with the proposed uses; therefore, no changes in the existing tolerances for livestock commodities are needed. The petitioner has submitted two liquid chromatography/mass spectroscopy/mass spectroscopy (L C - MS/MS) anal ytical methods for the determination of residues of the parent and its metabolites in/on plant and livestock commodities. BASF Method D0 603/02 was developed for determination of residues of saflufenacil and its metabolites M800H11 and M800H35 in different plant matrices using LC - MS/MS. The limit of quantitation (L OQ) was 0.01 ppm for each anal yt e in food matrices (human consumption) and 0.025 ppm for each anal yt e in feed matrices (livestock consumption). Th i s method w as used as the data - collection method in the anal ys is of samples for residues of concern from the various studies associated with the current petition. HED has determined that Method D0603/02 is a suitable enforcement method for plant commo dities as defined in Standard Operating Procedure (SOP) No. ACB - 019 (9/15/08). The submitted magnitude of the residue data for coffee, banana, and mango are adequate. There are also adequate storage stability data to validate the storage conditions and intervals of samples collected from the field trials. Quantifiable residues were not found in coffee RAC samples (green beans) even after application of saflufenacil at exaggerated rates (~3X); therefore, anal ys is of coffee processed fractions (roasted b eans, instant coffee) was not necessary and separate tolerances for processed fractions are not required.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 3 of 14 **Regulatory Recommendations and Residue Chemistry Deficiencies** Pending submission of a revised Section F (see requirements under Proposed Tolerances) , there are no residue chemistry

issues that would preclude granting permanent tolerances for residues of saflufenacil on the requested crops. The submitted data support: “Tolerances are established for residues of the herbicide saf lufenacil, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined b y measuring only the sum of saflufenacil (2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - diox o - 4 - (trifluoromethyl) - 1(2H ) - py rimidinyl] - 4 - fluoro -N

- [[methyl(1 - methylethyl)amino]sulfonyl]benzamide) and its metabolites N - [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl ) - 3,6 - dihydro - 1(2H ) - py rimidinyl) - 4 - fluorobenzo yl ] -N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbonyl )phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil, in or on the following commodities.” Coffee, green bean 0.03 ppm Banana 0.03 ppm Mango 0.03 ppm **Note to RD:** The se tolerance s should include a footnote stating “No U.S. registrations as of [date of FR notice].” 860.1550 Proposed Tolerances

 The petitioner is requested to submit a revised Section F specifying the revised definitions summarized above. A human - health risk assessm ent is forthcoming in a separate document (DP# 38 4 6 02 ). **Background** Saflufenacil is a broad - spectrum herbicide developed by BASF. It belongs to the herbicide mode - of - action Group 14 (cell membrane disruptors). Saflufenacil acts through the inhibition of PPO, resulting in cell membrane damage and subsequent plant death. Susceptible weeds develop sy mptoms within hours of application under active growing conditions. Plant death occurs within 3 - 5 day s depending upon growing conditions. The chemical structure and nomenclature of saflufenacil and its metabolites M800H11 and M800H35 , and the phys icochemical properties of the technical grade of saflufenacil, are presented in Tables 1 and 2. **T able**  **1. Saflufenacil**  **and Metabolite Nom**  **enclature.** Chemical Structure

Common name Saflufenacil Company experimental name BAS 800 H (synonyms : AC 433 379, BASF Reg. No. 4054449) Cl F N N O

O C H3 F F F O N H S N O O C H

3 C H 3 C H 3Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 4 of 14 **T able**  **1. Saflufenacil**  **and Metabolite Nom**  **enclature.** IUPAC name N ' - [2 - c hloro - 4 - fluoro - 5 - (3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2H ) - pyrimidinyl)benzoyl] -N

- isopropyl -N

- methylsulfamide CAS name 2 - c hloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2H ) - pyrimidinyl] - 4 - fluoro -N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide CAS registry number 372137 - 35 - 4 End -use product (EP) SharpenTM Powered by Kixor Herbicide (EPA Reg. No. 7969 - 278 ) ( 2. 85 lb ai/gal SC formulation) Chemical Structure

Common name M800H11 Chemical name N - [2 - c hloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2H ) - pyrimidinyl) - 4 - fluorobenzoyl] -N

' - isopropylsulfamide Chemical Structure

Common name M800H35 Chemical name N - [4 - c hloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea **T able**  **2. Physicochemical Properties of Technical Grade Saflufenacil.** Parameter Value Melting point Average = 189.9 ° C, peak max = 193.4 ° C pH 4.43 of 1% solution at 25 ° C Bulk Density (ambient temp.) 0.661 kg/L (free fall), 0.736 kg/L (packed) Water solubility (20°C) in g/100 mL: 0.0025 in water (pH = 5) ; 0.0014 in pH 4 buffer ; 0.21 in pH 7 buffer ; not determined due to degradation in pH 9 buffer Solvent solubility (20°C) in g/100 mL: 19.4 acetonitrile ; 24.4 dichloromethane ; 55.4 N,N - dimethylformamide ; 27.5 acetone ; 6.55 ethyl acetate ; 36.2 tetrahydrofuran ; 35.0 butyrolactone ; 2.98 methanol ; 0.25 isopropyl alcohol ; 0.23 toluene ; <0.01 1 - octano l; <0.005 n - heptane Va por pressure at 20/25°C 20 ° C = 4.5 x 10 - 15 Pa 25° C = 2.0 x 10 - 15 Pa Dissociation constant (pKa) 4.41 Octanol/water partition coefficient Mean Log P ow = 2.6 (P ow = 368.3) UV/visible absorption spectrum wavelength maximum: λmax = 271.6 nm extinction coefficient: ε = 9709 L/mol - cm Reference : BA SF Registration Document Number (DocID) 2005/1026464. **860.1200 Directions for Use** BASF has submitted a draft Brazilian label for the 70% WDG formulation ( Heat ® ) , which is representative of the Central and South American labels . Information pertaining to the proposed end - use product is listed in Table 3. A summary of the proposed use patterns is detailed in Table 4. Cl F N N H O

O F F F O N H S N H O O C H

3 C H 3

Cl F N H O

O N H S N H O O C H

3 C H 3 N H 2Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 5 of 14 **T able 3**  **. Summary of Proposed End**  **- Use Product.**  Trade Name Reg.

No. ai (% of formulation) Form

ulation Ty pe Target Crops Target Pests Label Date Heat® NA 7 0 WDG coffee, banana, and mango Broadleaf

weeds Draft label

submitted 11 /10 **Table 4. Summary of Directions for Use of**  **Saflufenacil .**  Applic. Timing, Ty pe, and Equip. Form

ulation App. rate

(lb ai/acre ) Max. No.

App. per Season Max. Seasonal

App. Rate (lb ai/acre ) PHI

(days) Use Directions and

Limitations Coffee, Banana, and Mango Ground directed to we eds Heat® 0.022 - 0.04 4 3 0. 131 7 ( coffee ) 15 (mango ) 30 (banana) Applications are to be

made in 1 6 - 43 gal/acre Note: A non - ionic adjuvant system is required for optimum activity . Conclusions : The submitted use directions for Heat ® are adequate to allow evaluation of the residue data relative to the proposed use s . **860.1300 Nature of the Residue**  **- Plants**  The previousl y- submitted metabolism data for corn, soy bean, and tomato were adequate to elucidate the nature of the residue in plants resulting from pre - plant/pre - emergence application. The main reactions involve d in the metabolic pathway of saflufenacil were N

- demethylation at the uracil ring , s tepwise degradation ( N - dealkylation) of the N

- methyl -N

- isopropyl group, hydrol ytic cleavage of the uracil ring generating a urea side chain , and hydrox yl ation of the phenyl ring. The HED ROCKS determined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 ( Memo, B. Daiss , 1/ 6 /0 9 ; D 359645 ) . This conclusion was translated to perennial crops (i.e. , tree fruits and tree nuts) where saflufenacil application is directed to the weeds on the orchard floor ( Memo, G. Kramer , 7 /22 /09; D 349938 ). As the proposed use on coffee, banana, and mango is also directed to weeds at the base of the plants, HED concludes that the residues of concern for the tolerance expression and risk assessment also consist of saflufenacil, M800H11, and M800H35 for these crops. **860.1300 Nature of the Residue -**  **Livestock /**  **860.1480 Meat, Milk, Poultry, and Eggs** The nature of the residue in livestock is adequately understood based on acceptable metabolism studies conducted on lactating goats and laying hens. There are no livestock feedstuffs associated with the proposed uses; therefore, no changes in the existing tolerances for livestock c ommodities are needed. **860.1340 Residue Analytical Methods** BASF Method D0603/02 is the current enforcement method for determination of residues of saflufenacil and its metabolites M800H11 and M800H35 in different plant matrices. Residues of saflufenacil and its metabolites M800H11 and M800H35 were extracted with methanol:water (70:30; v:v). The methanol extract was evaporated and reconstituted in methanol:water (50:50;Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 6 of 14 v:v) for LC - MS/MS analy sis. Two transitions per anal yt e were monitored f or the quantitation and confirmation of saflufenacil, M800H11 and M800H35. The residues of each anal yt e were expressed as parent equivalents using a molecular weight conversion factor (1.0 for saflufenacil, 1.06 for M800H11 , and 1.42 for M800H35). The LO Q was 0.01 ppm for each analy te. The limit of detection (L OD) was reported to be 3X the standard deviation (SD) at the LOQ for each anal yt e (0.002 - 0.003 ppm) . Recovery samples, prepared at levels of LOQ and 10 X LOQ in each matrix, were generally within the acceptable range of 70 - 120%. **860.1360 Multiresidue Methods (MRM)**  Saflufenacil and its metabolites M800H11 and M800H35 were screened through the MRM described in the United States Food and Drug Administration (FDA) Pesticide Anal ytical Manual, Vol. I (PAM I). Saflufenacil and the metabolites were tested using procedures outlined in Protocols B, C, D, E , and F of the MRM. All Protocols B, C, D, E , and F were found to be unsuitable for determination of residues of saflufenacil and its metabolites M80 0H11 and M800H35. Since the analy tes are not N

- methyl - carbamates, naturally fluorescent or substituted urea derivatives, the tests using Protocol A and G were not performed. **860.1380 Storage Stability** Storage stability

data have been submitted for residues of saflufenacil and its metabolites M800H11 and M800H35 in/on various crop commodities [corn (grain, forage, stover); so yb ean (seed, forage, hay); orange (fruit, pulp, juice, oil); radish (root); grape (raisin); and garbanzo bean (seed)] indicating that residues of saflufenacil, M800H11, and M800H35 are stable in/on all tested commodities during frozen storage for up to 548 days ( MRID No. 47523801 ). There are no unresolved s torage stability issues , and no corrections need to be applied to the vari ous magnitude of the residue studies . **860.1500 Crop Field Trials** Banana DER Reference List 48239801 .der.doc 48239802 .der.doc 4823980 3 .der.doc **MRID No. 48239801** : BASF Corporation has submitted field trial data for saflufenacil on banana. Two banana field trials were conducted during the 2008 growing season in Brazil. Each trial location consisted of one untreated and one treated plot. Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A ( 1 X) directed to the base of the plants, with a 3 0 - day retreatment interval (RTI), for a total appl ication rate of 0.131 lb ai/A (1X). The applications were made using ground equipment with 21 gallons per acre (GPA) spray

volumes. An adjuvant (surfactant, Dash ® ) was included in the spray mixture. Samples of mature bananas were harvested at a 30 - day PHI.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 7 of 14 The results from these trials on banana show that after three applications of saflufenacil at 0.044 lb ai/A (0.049kg ai/ha), residues of saflufenacil, M 800H11, and M800H35 were below the LOQ (<0.01 ppm each) in banana samples harvested at a 30 - day PHI. Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm . **MRID No. 48239802:** BASF Corporation has submitted field trial data for saflufenacil on banana. Two banana field trials were conducted during the 2010 growing season in Brazil. Each trial location consisted of one untreated and one treated plot. Each treated plot received five applications of the 70% WDG formulation of saflufenacil at 0.0667 lb ai/A ( 1.5X) directed to the base of the plants, with a 3 - week RTI, for a total application rate of 0.333 lb ai/A ( 2.5X). The applications were made using ground equipment with 21 GPA spray volumes. An adjuvant (surfactant , Dash ® ) was included in the spray mixture. Samples of mature bananas were harvested at 0 - and 1 - day PHI s. The results from these trials on banana show that after five applications of saflufenacil at 0.0667 lb ai/A (0.0749 kg ai/ha), residues of safluf enacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in banana samples harvested at 0 - and 1 - day PHIs. Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm . **MRID No. 48239803:** BASF Corporation has submitted field trial data for saflufenacil on banana. A total of 10 field trials were conducted on bananas during the 2008 growing season in Costa Rica (2 trials), Colombia (1 trial), Ecuador (3 trials), Guatemala, (1 trial), Hondu ras (2 trials), and Panama (1 trial). Each trial location consisted of one untreated and one treated plot. Each treated plot received five applications of the 70% WDG formulation of saflufenacil directed to the base of the plants at 0.064 - 0.071 lb ai/A ( 1.5X - 1.6X), with 11 - to 28 - day retreatment intervals (RTI s), for a total application rate of 0.33 - 0.35 lb ai/A/season ( 2.8X - 3.0X). The applications were made using ground equipment with approximately 20 - 23 GPA spray

volumes. An adjuvant [ crop - oil concentrate (COC) ] was included in the spray mixture, together with ammonium sulfate (AMS) fertilizer. Duplicate s amples of commercially mature banana were harvested at a 0 - or 1 - day PHI . The results from these trials on banana show that after five applications of saflufenacil directed to the base of the plants at 0.067 lb ai/A/application (0.075 kg ai/ha/application), for a total seasonal rate of 0.33 lb ai/A (0.375 kg ai/ha), maximum saflufenacil, M800H11, and M800H35 residues were <LOQ (<0.01 ppm each) in/on banana whole fruit samples harvested at a 0 - day PHI(n=20) or 1 - day

PHI (n=20). Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm at the 0 - and 1 - day PHI s. **TABLE 5**  **. Summary of Residue Data from** **Crop Field Trials with Banana**  **( MRID**  **#s 482398**  **01 thru -**  **03 )**  **.** Commodity Total Applic.

Rate (lb ai/A) [kg ai/ha] PHI

(days) Analyte Residue Levels (ppm) 1 n Min. Max. HAFT 2 Median Mean Std. Dev. Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate , 30 - Day PHI Banana 0.33 - 0.35

[0.372 - 0.392] 0 Saflufenacil 2 2 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 -Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 8 of 14 **TABLE 5**  **. Summary of Residue Data from** **Crop Field Trials with Banana**  **( MRID**  **#s 482398**  **01 thru -**  **03 )**  **.** Commodity Total Applic.

Rate (lb ai/A) [kg ai/ha] PHI

(days) Analyte Residue Levels (ppm) 1 n Min. Max. HAFT 2 Median Mean Std. Dev. Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate , 30 - Day PHI Banana 0.33 - 0.35

[0.372 - 0.392] 1 Saflufenacil 2 2 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 - Banana 0.131

[0.147] 30 Saflufenacil 2 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 - 1 For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (< LOQ) were considered to be 0.01 ppm (LOQ). 2 HAFT = highest - average field trial. 3 Combined residues of saflufenacil (parent + M800H11 + M800H35). Conclusions : The submitted residue data are adequate to fulfill data requirements for bananas imported from Central/South America . Even though all major exporting countries were not represented (Table 6 ) , HED will not require additional data as all residues were <LOQ , even at ~3X exaggerated use rate . Also, HED generall y requires residue data for both bag ged and unbagged bananas. The fruit in these trials were “grown and maintained according to typical agricultural practices for each region ,” which HED interprets to mean bagged. As saflufenacil is not applied directl y to the plants and there is no eviden ce of s ys temic activity in fruit/tree crops, additional data on un - bagged bananas will not be required. The available data will thus support the proposed use pattern. **TABLE 6**  **. Trial Numbers and Geographical Locations**  . Country Banana Submitted Requested 1 U.S. Brazil 4 Columbia 1 2 Costa Rica 2 3 Ecuador 3 3 Guatemala 1 0 Honduras 2 2 Mexico 0 2 Panama 1 0 Total 1 4 12 1 The requested number and geographic distribution of field trials for bananas, according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05. The residue data for bananas were not entered into the OECD MRLCalculator as all of the residues were <LOQ. The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35 , expressed as parent equivalents, is 0. 0 3 ppm for banana .Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 9 of 14 Coffee DER Reference List 4823980 4 .der.doc 4823980 5 .der.doc **MRID No. 48239804:** BASF Corporation has submitted field trial data for saflufenacil on coffee. Three coffee field trials were conducted during the 2008 growing season in Brazil. Each trial location consisted of one untreated and one treated plot. Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A ( 1X) directed to the base of the plants, with a 4 - week RTI , for a total application rate of 0.131 lb ai/A ( 1X). The applications were made using ground equipment with 21 GPA spray volumes. An adjuvant (surfactant, Dash ® ) was included in the spray mixture. Samples of mature coffee beans were harvested at a 7 - day

PHI . The results from these trials on coffee show that after three applications of saflufenacil at 0.044 lb ai/A (0.049 kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in coffee samples harvested at a 7 - day PHI. Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm . **MRID No. 48239805:** BASF Corporation has submitted field trial data for saflufenacil on coffee. Five coffee field trials were conducted during the 2008 growing season in Costa Rica (2 trials), Colombia (2 trials), and Mexico (1 trial) . Each trial location consisted of one untreated and one treated plot. Each treated plot received four applications of the 70% WDG formulation of saflufenacil at 0.087 - 0.092 lb ai/A ( 2.0 - 2.1X) directed to the base of the plants, with 8 - to 35 - day RTIs, for a total application rate of 0.35 - 0.36 lb ai/A ( 2.7X) . The applications were made using ground equipment with 21 - 22 GPA spray volumes. An adjuvant ( COC ) was included in the spray mixture. Sampl es of mature coffee beans were harvested at 0 - day or 1 - day PHI s . The results from these trials on coffee show that after four applications of saflufenacil (70% WDG) directed to the base of the plants targeting 0.087 lb ai/A/application (0.098 kg ai/ha/a pplication), for a total seasonal rate of 0.35 lb ai/A (0.392 kg ai/ha), maximum saflufenacil, M800H11, and M800H35 residues were <L OQ (<0.01 ppm each) in/on coffee green bean samples harvested at a 0 - day PHI (n=10) or 1 - day

PHI (n=10). Therefore, the max imum combined residues of saflufenacil and its metabolites was <0.03 ppm at the 0 - or 1 - day PHI . **TABLE 7**  **. Summary of Residue Data from** **Crop Field Trials with Coffee (** **MRID #s**  **482398 04 and**  **- 0**  **5) .**  Commodity Total Rate (lb

ai/A) [ g ai/ha] PHI

(days) Analyte Residue Levels (ppm) 1 n Min. Max. HAFT 2 Median Mean Std. Dev. Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate , 7 - Day PHI Coffee, green bean 0.3 5 - 0.36

[ 392 - 400 ] 0 Saflufenacil 10 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 - 0.3 5 - 0.36 [ 392 - 400 ] 1 Saflufenacil 10 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 < 0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 -Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 10 of 14 **TABLE 7**  **. Summary of Residue Data from** **Crop Field Trials with Coffee (** **MRID #s**  **482398 04 and**  **- 0**  **5) .**  Commodity Total Rate (lb

ai/A) [ g ai/ha] PHI

(days) Analyte Residue Levels (ppm) 1 n Min. Max. HAFT 2 Median Mean Std. Dev. Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate , 7 - Day PHI Coffee, green bean 0.131

[0.147] 7 Saflufenacil 3 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 <0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 < 0.03 <0.03 <0.03 <0.03 - 1 For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (<LOQ) were considered to be 0.01 ppm (LOQ). 2 HAFT = highest - average field trial. 3 Combined residues of saflufenacil (parent + M800H11 + M800H35). Conclusions : The submitted residue data are adequate to fulfill data requirements for coffee imported from Central/South America . Even though all major exporting countries were not repres ented (Table 8 ) , HED will not require additional data as all residues were <LOQ , even at ~3X exaggerated use rate . The available data will thus support the proposed use pattern. **TABLE 8**  **. Trial Numbers and Geographical Locations**  . Country Coffee Submitted Requested 1 U.S. Brazil 3 1 Columbia 2 1 Costa Rica 2 1 Guatemala 0 1 Indonesia 0 1 Mexico 1 1 Vietnam 0 1 Total 8 7 1 The requested number and geographic distribution of field trials for coffee, according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05 and import data (http://www.ers.usda.gov/Data/FoodImports/Data/2011/CoffeeT1.xls and http://www.nationmaster.com/graph/eco_tra_wit_us_us_imp_of_gre_cof - trade - us - imports - green - coffee ). All countries (in which the pe sticide is marketed or intended to be marketed) must be represented if the amount that they export to North America represents 5% or more of imports of the subject crop into any of the country in which a tolerance is being sought. The residue data for co ffee were not entered into the OECD MRLCalculator as all of the residues were <LOQ. The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35, expressed as parent equivalents, is 0.03 ppm for coffee , green bean . Mango DER Reference List 4823980 6 .der.doc 4823980 7 .der.doc **MRID No. 48239806 :**  BASF Corporation has submitted field trial data for saflufenacil on mango. Two mango field trials were conducted during the 2008 growing season in Brazil. Each trial location consisted of one untreated and one treated plot. Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A ( 1X) directed to the base of the tree s, with a 10 - day RTI, for a total application rate of 0.131 lb ai/A ( 1X). TheSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 11 of 14 applications were made using ground equipment with 21 GPA spray volumes. An adjuvant (surfactant, Dash ® ) was included in the spray mixture. Samples of mature mango were harvested at a 14 - or 15 - day PHI . The results from these trials on mango show that after three applications of saflufenacil at 0.044 lb ai/A (0.049kg ai/ ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in mango samples harvested at a 14 - or 15 - day PHI. Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm . **MRID No. 48239807 :**  BASF Corporation has submitted field trial data for saflufenacil on mango. Two mango field trials were conducted during the 200 8 - 2009 growing season in Brazil. Each trial location consisted of one untreated and one treated plot. Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A ( 1X) directed to the base of the tree s, with a 10 - day RTI, f or a total application rate of 0.131 lb ai/A ( 1X). The applications were made using ground equipment with 21 GPA spray volumes. An adjuvant (surfactant, Dash ® ) was included in the spray mixture. Samples of mature mango were harvested at a 15 - day

PHI. The results from these trials on mango show that after three applications of saflufenacil at 0.044 lb ai/A/ application (0.049kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in mango samples harvested at a 15 - d ay PHI . Therefore, the maximum combined residues of saflufenacil and its metabolites w as <0.03 ppm. **TABLE 9**  **. Summary of Residue Data from** **Crop Field Trials with Mango**  **.** Commodity Total Applic.

Rate (lb ai/A) [kg ai/ha] PHI

(days) Analyte Residue Levels (ppm) 1 n Min. Max. HAFT 2 Median Mean Std. Dev. Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate , 15 - Day PHI Mango 0.131

[0.147] 14 - 15 Saflufenacil 4 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H11 <0.01 <0.01 <0.01 <0.01 <0.01 - M800H35 < 0.01 <0.01 <0.01 <0.01 <0.01 - Combined 3 <0.03 <0.03 <0.03 <0.03 <0.03 - 1 For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (<LOQ) were considered to be 0.01 ppm (LOQ). 2 HAFT = highest - average field trial. 3 Combined residues of saflufenacil (parent + M800H11 + M800H35). Conclusions : The submitted residue data are adequate to fulfill data requirements for m ango imported from Central/South America . Even though all major exporting countries were not represented (Table 1 0 ) , HED will not require additional data as all residues were <LOQ. The available data will thus support the proposed use pattern.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 12 of 14 **TABLE 10**  **. Trial Numbers and Geographical Locations**  . Country Mango Submitted Requested 1 U.S. Brazil 4 1 Ecuador 0 1 Mexico 0 1 Peru 0 1 Total 4 4 1 The requested number and geographic distribution of field trials for mango , according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05 and import data (Fruit and Tree Nuts Situation and Outlook Yearbook (USDA, 2008)). All countries (in which the pe sticide is marketed or intended to be marketed) must be represented if the amount that they export to North America represents 5% or more of imports of the subject crop into any of the country in which a tolerance is being sought. The residue data for m ango were not entered into the OECD MRLCalculator as all of the residues were <LOQ. The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35, expressed as parent equivalents, is 0.03 ppm for mango . **860.1520 Processed Food and Feed** Coffee BASF requested a waiver for residue data for s aflufenacil in/on coffee processed fractions . HED has previousl y reviewed process ing studies for s aflufenacil when applied postemergence directed under the leaf canopy at the base of fruit tree crops: apple (MRID 47128229), orange (MRID 47128228), plum (MRID 47128230), and grape (MRID 47128232). Inall of these studies , the individual residues of s aflufenacil and its metabolites M800H11 and M800H35 were < LOQ (i.e., 0. 01 ppm for each anal yt e) in/on unwashed RAC samples of apple, orange, plum and grape after application of s aflufenacil at exaggerated rates of 2 - 5X. Since quantifiable residues were not found in the whole fruit RAC samples, analysis of the processed commo dities were not necessary (except for orange - residues in citrus oil were also <LOQ) . A similar conclusion can be reasonabl y expected for coffee when s aflufenacil is applied postemergence - directed beneath the leaf canop y of coffee plants. Quantifiable re sidues were not found in coffee RAC samples (green beans) even after application of s aflufenacil at exaggerated rates (~3X) ; therefore , anal ys is of coffee processed fractions (roasted beans, instant coffee) i s not necessary and separate tolerances for processed fractions are not required. **860.1650 Submittal of Analytical Reference Standards** Analy tical standards of saflufenacil (expiration date: 2/1/ 13 ) , M800H11 (expiration date: 7/1/ 1 4 ) , and M800H35 (expiration date: 7/1/ 14 ) are currently available in the National Pesticide Standards Repository [ s ource: personal communication with T . Cole of AC L/BEAD , 6 /2 0 / 1 1 ] . **860.1850/860.1900 Confined/Field Accumulation in Rotational Crops** Rotational crop studies are not germane to this petition as coffee, banana, and mango are notSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 13 of 14 rotated with other crops. **860.1550 Proposed Tolerances** A summary

of the recommended tolerances for the current petition are listed in Table 11 . The petitioner should submit a revised section F reflecting the corrected commodity definitions. There are no Canadian or Codex maximum residue limits (MRL s) established for residues of s aflufenacil and its metabolite s in coffee, banana, and mango commodities. H armoniz ation i s thus not an issue for this petition . **Table 11**  **. Tolerance Summary for**  **Saflufenacil .**  Commodity Proposed Tolerance (ppm) HED - Recommended

Tolerance (ppm) Correct Commodity

Definition

/Comments Coffee, green bean 0.03 0.03 Banana, whole fruit 0.03 0.03 Banana Mango, fruit 0.03 0.03 Mango **Note to RD:** The se tolerance s should include a footnote stating “No U.S. registrations as of [date of FR notice].”

**Attachments:** International Residue Limit Status (IRLS) sheet .

cc: G. Kramer (RAB1) RDI: RAB1 Chemists ( 7 / 13 / 1 1 ) G.F. Kramer:S10 95 7:PY - S :(703)305 - 5079:7509P:RAB1Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 390922

Page 14 of 14 

### IRLS Sheet. Saflufenacil (118203; Date of Request: 06/20/2011) Summary of U . S . and International Tolerances and Maximum Residue Limits Residue Definition : U . S . Canada Mexico 2 Codex 40 CFR 180. 64 9: Plant: saflufenacil, including its metabolites and degradates, sum of saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2H ) -pyrimidinyl] - 4 - fluoro -N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide, and its metabolites N

- [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro 1(2H ) -pyrimidinyl) - 4 - fluorobenzoyl] -N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbon yl)phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil Livestock: saflufenacil 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2H

) - pyrimidinyl] - 4 - fluoro -N

- [[methyl(1 - methylethyl)amino]sulfonyl]benz amide, including the metabolites N' - {2 - chloro - 4 - fluoro - 5 - [1,2,3,6 - tetrahydro - 2,6 - dioxo - 4 - (trifluoromethyl)pyrimidin - 1 - yl]benzoyl} -N

- isopropyl sulfamide and N

- [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl] amino}carbonyl)phenyl]urea Livestock: 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2H

) - pyrimidinyl] - 4 - fluoro -N

- [[methyl(1 - methylethyl)amino]sulfonyl]benz amide None

Commodity 1 Tolerance (ppm)/Maximum Residue Limit (mg/kg) U . S . Canada Mexico 2 Codex Coffee, green bean 0.03 Banana, whole fruit 0.03 Mango, fruit 0.03 Completed: M. Negussie; 06/21/2011 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts U . S . tolerances and/or Codex MRLs for its export purposes.